Cloth simualtion (pinning) multiple times on the same model
For such a model it should be sufficient to model it by hand using the cloth simulation would be a task too complicated for a model such as this. Using box modeling strategy and maybe subdividing the faces would suffice.

This is Unless you will be animating the model too, then cloth sim is the way to go.


Define the basic form of your model.

You will want to apply Edge Crease at the top and bottom of the model.
Apply a subdivision modifier.